Malic acid

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H6O5
Molecular Weight	134.0874
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(CC(O)=O)C(O)=O

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C4H6O5
Molecular Weight	134.0874
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://gov.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/FR330.pdf | https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdfhttp://www.cosmeticsinfo.org/ingredient/sodium-malate | https://www.food.gov.uk/science/additives/enumberlist#h_7 | https://www.ncbi.nlm.nih.gov/pubmed/11358110 | https://www.ncbi.nlm.nih.gov/pubmed/9477166

Malic acid is a tart-tasting organic dicarboxylic acid that contributes to the taste of many sour or tart foods such as apples. Sodium Malate is the sodium salt of Malic Acid. Malic Acid and Sodium Malate can be found in a wide range of cosmetics and personal care products. Sodium Malate functions as a skin conditioning agent-humectant. As a food additive, Sodium Malate has the E number E350. Sodium Malate has demonstrated protective effect on cisplatin-induced toxicity in mice. Sodium malate could become a useful agent for the reduction of CDDP-induced toxicity, particularly nephrotoxicity and hepatotoxicity.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cisplatin-induced toxicity 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9477166 https://www.ncbi.nlm.nih.gov/pubmed/9514605	Secondary	Preclinical	Unknown Approved Use Unknown
Cardiac arrhythmia 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8974556 https://www.ncbi.nlm.nih.gov/pubmed/1458176	Preventing	Preclinical	Unknown Approved Use Unknown
Skin injuries 8 Sources: https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdf	Curative	Approved 8429	ACERBINE Approved Use Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.

PubMed

Title	Date	PubMed
Metabolic regulation of pH in plant cells: role of cytoplasmic pH in defense reaction and secondary metabolism.	2001	11407758
Inhibiting expression of a tomato ripening-associated membrane protein increases organic acids and reduces sugar levels of fruit.	2001 Apr	11346954
Phlebotomine sandflies in Venezuela. V. Review of the genus Brumptomyia (Diptera: Psychodidae), with description of the female of Brumptomyia devenanzii, re-description of the male and isozymatic profile.	2001 Apr	11339889
Differential gene expression in the small intestines of wildtype and W/W(V) mice.	2001 Apr	11298995
Skeletal muscle oxidative capacity and exercise tolerance in rats with heart failure.	2001 Apr	11283428
Contribution of cryofixation and freeze-substitution to analytical microscopy: a study of Tritrichomonas foetus hydrogenosomes.	2001 Apr 1	11279674
Effect of an antidiabetic extract of Catharanthus roseus on enzymic activities in streptozotocin induced diabetic rats.	2001 Aug	11448549
Carbohydrate deprivation reduces NADPH-production in fish liver but not in adipose tissue.	2001 Aug	11404182
Abscisic acid induces a decline in nitrogen fixation that involves leghaemoglobin, but is independent of sucrose synthase activity.	2001 Feb	11283173
Identification in Saccharomyces cerevisiae of two isoforms of a novel mitochondrial transporter for 2-oxoadipate and 2-oxoglutarate.	2001 Jan 19	11013234
Acetate as a carbon source for hydrogen production by photosynthetic bacteria.	2001 Jan 23	11164959
Inducible and constitutive expression using new plasmid and integrative expression vectors for Thermus sp.	2001 Jun	11412354
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001 Jun	11405809
Energetic determinants of tyrosine phosphorylation of focal adhesion proteins during hypoxia/reoxygenation of kidney proximal tubules.	2001 Jun	11395393
A pre-genetic study of the isoforms of malic enzyme associated with lipid accumulation in Mucor circinelloides.	2001 Jun	11390681
The homeodomain proteins PBX and MEIS1 are accessory factors that enhance thyroid hormone regulation of the malic enzyme gene in hepatocytes.	2001 Jun 29	11331288
Myxothiazol induces H(2)O(2) production from mitochondrial respiratory chain.	2001 Mar 2	11237706
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.	2001 May	11440113
Aluminum activates a citrate-permeable anion channel in the aluminum-sensitive zone of the maize root apex. A comparison between an aluminum- sensitive and an aluminum-resistant cultivar.	2001 May	11351102
Relationship between allozyme genotype and sensitivity to stressors in the western mosquitofish Gambusia affinis detected for elevated temperature but not mercury.	2001 May	11239682
Method validation and determinations of levofloxacin, metronidazole and sulfamethoxazole in an aqueous pharmaceutical, urine and blood plasma samples using quantitative nuclear magnetic resonance spectrometry.	2012 Jan 15	22265475
The virucidal effect against murine norovirus and feline calicivirus as surrogates for human norovirus by ethanol-based sanitizers.	2013 Aug	23135829
The virucidal effects against murine norovirus and feline calicivirus F4 as surrogates for human norovirus by the different additive concentrations of ethanol-based sanitizers.	2016 Mar	26482918

Patents

Sample Use Guides

In Vivo Use Guide

Apply Acerbine solution (malic acid, salicylic acid, benzoic acid) to the wound or damaged skin two or more times daily or moisten the dressing again. Once scar formation begins, one application a day is generally sufficient.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:34 GMT 2023`
Record UNII	817L1N4CKP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Malic acid

Official Name

English

MALIC ACID [USP IMPURITY]

Common Name

English

MALIC ACID, DL-

Common Name

English

POMALOUS ACID

Common Name

English

INS NO.296

Code

English

MALIC ACID [VANDF]

Common Name

English

MALATE

Common Name

English

MALIC ACID [INCI]

Common Name

English

MALIC ACID [USP-RS]

Common Name

English

DL-MALIC ACID

Common Name

English

HYDROXYBUTANEDIOIC ACID, (±)-

Systematic Name

English

MALIC ACID [FCC]

Common Name

English

E-296

Code

English

NSC-25941

Code

English

INS NO. 296

Code

English

E296

Code

English

(±)-MALIC ACID

Common Name

English

MALIC ACID [II]

Common Name

English

MALIC ACID [EP MONOGRAPH]

Common Name

English

HYDROXYBUTANEDIOIC ACID [HSDB]

Common Name

English

INS-296

Code

English

MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]

Common Name

English

D,L-MALIC ACID

Common Name

English

Malic acid [WHO-DD]

Common Name

English

HYDROXYSUCCINIC ACID

Common Name

English

MALIC ACID [MI]

Common Name

English

2-HYDROXYBUTANEDIOIC ACID

Systematic Name

English

MALIC ACID [NF]

Common Name

English

Classification Tree Code System Code

CODEX ALIMENTARIUS (GSFA)

INS-296